Name: Berkshires Untold
Price range: CA $172

Your Sheffield Vacation

The stress-free way to experience this unique city is with a custom-made Sheffield vacation package. Stay in the neighborhood of Canann Village Historic District, which is great for dining, culture and shopping or go someplace else — our package deals are all about you. Fill your free time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you really should see during a trip to Sheffield. Don't delay exploring this city any longer. Your ultimate Sheffield vacation is only a few clicks away with Expedia.

Top Sheffield Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Hilton Albany

Downtown Albany

CA $1,009

per person

Jul 31 - Aug 2

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

7.2/10 Good! (1,004 reviews)

The Hilton hotel was cleaned I had a excellent experience I would recommend it

Reviewed on May 9, 2026

Hampton Inn Albany-Wolf Road (Airport)

CA $1,042

per person

Jul 31 - Aug 2

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

8.8/10 Excellent! (1,004 reviews)

The breakfast menu was fresh. The staff replenished the food as it ran out. The food area was clean and organized.

Reviewed on May 16, 2026

Park Manor Hotel

CA $1,128

per person

Jul 31 - Aug 2

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

7.8/10 Good! (1,285 reviews)

It’s ok for the price, but property condition is rough and it needs deep clean.

Reviewed on May 16, 2026

Hampton Inn & Suites Albany-Downtown

Downtown Albany

CA $1,051

per person

Jul 31 - Aug 2

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

8.8/10 Excellent! (1,060 reviews)

We had to switch rooms due to a leaking shower. Somehow it was leaking into the room. Additionally the shower was “handicap” accessible but also sprayed water all over the bathroom floor. However they immediately moved us upon complaint.

Reviewed on Apr 20, 2026

Best Western Plus Franklin Square Inn Troy/Albany

CA $1,129

per person

Jul 31 - Aug 2

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

8.8/10 Excellent! (1,004 reviews)

Very close to Troy Theater, nice location , beautiful view of water & right next to a BBQ place .

Reviewed on May 12, 2026

Ready to book your vacation to Sheffield?

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Sheffield Hotel Deals

Wilder House Berkshires

48 S Main Street Sheffield MA

Fully refundableReserve now, pay when you stay

CA $226

CA $252 total

May 20 - May 21

includes taxes & fees

9.8/10 Exceptional! (48 reviews)

Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)

Reviewed on May 11, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

CA $121

CA $165 total

May 24 - May 25

includes taxes & fees

9/10 Wonderful! (938 reviews)

Nice for families, has kitchen facilities for cooking. Door to room needs attention. Had to slam hard to close. Nice big bathroom. Thought we were getting 2 beds but had king bed and pull out couch. Wouldn’t always work for everyone. Could hear dog barking in nearby room. Price was right

Reviewed on May 17, 2026

Berkshires Untold

194 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

CA $172

CA $192 total

May 20 - May 21

includes taxes & fees

See all 1,298 properties in Sheffield

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.